will not undergo reaction very easily though it is a primary halide. In the light of the above statements, choose the most appropriate answer from the options given below :- ABoth Statement I and Statement II are incorrect
- BBoth Statement I and Statement II are correct
- CStatement I is correct but Statement II is incorrect
- DStatement I is incorrect but Statement II is correct
View written solutionFree
Correct answer: B
-
Identify the substrate
The compound is chloromethyl methyl ether:
The carbon bearing chlorine is primary, but it is also adjacent to oxygen.
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Examine Statement I: It undergoes though it is a primary halide
Normally, primary halides do not undergo because formation of a primary carbocation is unstable.
But here, loss of gives a cation next to oxygen:
This cation is stabilized by resonance with the lone pair on oxygen:
Thus, the intermediate is not an ordinary unstable primary carbocation; it is resonance-stabilized oxonium/carboxonium-type cation.
Therefore, is possible.
So, Statement I is correct.
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Examine Statement II: It will not undergo very easily though it is a primary halide
At first glance, a primary halide should favor .
However, in this molecule, the carbon attached to chlorine is bonded to an oxygen-containing group:
Oxygen exerts a strong effect, making the carbon electrophilic, but the adjacent oxygen also affects backside attack because the substrate is a type of alkoxy methyl halide, where the reaction pathway can be influenced by neighboring electronic effects and easier ionization.
More importantly, such compounds are known to undergo substitution not predominantly by a simple easy route; due to stabilization of the cation by oxygen, becomes unusually favorable, and is not very easy compared with normal primary alkyl halides.
Hence, Statement II is also correct.
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Conclusion
- Statement I: Correct
- Statement II: Correct
Therefore, the correct option is:
-
Comparison with stored answer
Stored correct answer: B
My derived answer: B
So, they agree.
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